1. Heroes Gala

Up from #2
This black-tie optional event is introducing a new brand identity this year to cement its place among must-attend Toronto galas. After surpassing its 2018 fund-raising goal of $2 million, the event in support of Right to Play is aiming closer to $3 million this year, with 1,200 sports-minded attendees. Sun Life Financial is the new title sponsor. Next: October 17, 2019
This black-tie optional event is introducing a new brand identity this year to cement its place among must-attend Toronto galas. After surpassing its 2018 fund-raising goal of $2 million, the event in support of Right to Play is aiming closer to $3 million this year, with 1,200 sports-minded attendees. Sun Life Financial is the new title sponsor. Next: October 17, 2019
Photo: Scott Ramsay for Right to Play
2. Grand Cru Culinary Wine Festival

With a fund-raising goal of $5 million, this year’s philanthropic foodie event includes an extra day and a live auction, as it does every other year. The auction should draw about 500 bidders at the Beanfield Centre, while the exclusive dinners at 25 private homes and venues should attract about 900. Auction lots include a luxury vehicle and rare wines. Next: November 1-2, 2019
Photo: Courtesy of University Health Network
3. True Patriot Love Gala

With attendance holding steady at 1,000, this fund-raiser for Canadian veterans and military families will celebrate 11 years at the Metro Toronto Convention Centre in November. Attendees enjoyed cocktails, dinner, and dancing last year, raising $1.4 million. This year’s goal, when Bell returns as the presenting sponsor, is $1.5 million. Next: November 7, 2019
Photo: A.J. Leitch
4. Teddy Bear Affair

Attendance grew from 850 people in 2017 to more than 900 last year, when the gala sold out and attendees raised $1.8 million in support of the Children’s Aid Foundation of Canada. The dinner and dance takes place at the Metro Toronto Convention Centre, and RBC is the new patron sponsor. Next: November 2, 2019
Photo: Lily Leung
5. Toronto Taste

Up from #9
This benefit for Second Harvest’s food rescue program moved to the Evergreen Brickworks in 2019 and sold more tickets (1,500) than in any of the past three years. The theme was “vintage circus,” with stilt walkers and jugglers entertaining the crowd as they snacked on fare from 50 of the city’s top chefs. Daniels Corp. was the presenting sponsor. Next: June 14, 2020
This benefit for Second Harvest’s food rescue program moved to the Evergreen Brickworks in 2019 and sold more tickets (1,500) than in any of the past three years. The theme was “vintage circus,” with stilt walkers and jugglers entertaining the crowd as they snacked on fare from 50 of the city’s top chefs. Daniels Corp. was the presenting sponsor. Next: June 14, 2020
Photo: Ryan Emberley
6. Power Plant Contemporary Art Gallery’s Power Ball

Up from #8
This hedonistic and edgy art gala raised more than $330,000 for the Power Plant in 2019, with attendance level at 1,300 and a “speakeasy” theme inspired by the 21 Club for the event’s 21st year. High-end department store Holt Renfrew was the new presenting sponsor. Next: June 4, 2020 See more: This Toronto Art Benefit Took Guests to a Surreal Speakeasy
This hedonistic and edgy art gala raised more than $330,000 for the Power Plant in 2019, with attendance level at 1,300 and a “speakeasy” theme inspired by the 21 Club for the event’s 21st year. High-end department store Holt Renfrew was the new presenting sponsor. Next: June 4, 2020 See more: This Toronto Art Benefit Took Guests to a Surreal Speakeasy
Photo: Brilynn Ferguson
7. Jays Care Foundation's Curve Ball

This charity supporting children and youth in the Jays Care program pared back the number of tables at its gala dinner, with 1,280 attendees raising over $1.5 million. Highlights included rubbing shoulders with the entire Blue Jays roster and experiencing the newly laid out on-field event space at the Rogers Centre. Next: June 2020
Photo: George Pimentel
8. Rally for Kids

Up from #10
This gala, draft night, and rally car race-cum-scavenger-hunt raised more than $850,000 in support of the Pinball Clemons Foundation in 2018 when celebrity drivers included Entourage actor Adrian Grenier. Highlights included an escape room in an Air Canada plane and a red-carpet party at Hotel X. Platinum Cars returned as a sponsor. Next: October 18-19, 2019
This gala, draft night, and rally car race-cum-scavenger-hunt raised more than $850,000 in support of the Pinball Clemons Foundation in 2018 when celebrity drivers included Entourage actor Adrian Grenier. Highlights included an escape room in an Air Canada plane and a red-carpet party at Hotel X. Platinum Cars returned as a sponsor. Next: October 18-19, 2019
Photo: Courtesy of Solutions With Impact
9. What's On the Table

Up from #11
The Stop Community Food Centre brings its fund-raiser back to the Art Gallery of Ontario in 2019, when organizers aim to raise $400,000 through live and silent auctions. Last year saw more than 30 top chefs and wineries serve creative dishes to 400 young professionals and food lovers. Stonegate Private Counsel returned as a sponsor. Next: November 20, 2019
The Stop Community Food Centre brings its fund-raiser back to the Art Gallery of Ontario in 2019, when organizers aim to raise $400,000 through live and silent auctions. Last year saw more than 30 top chefs and wineries serve creative dishes to 400 young professionals and food lovers. Stonegate Private Counsel returned as a sponsor. Next: November 20, 2019
Photo: Courtesy of Gabriel Li Photography
10. Canfar's Bloor Street Entertains

Up from #12
Fund-raising grew at last year’s end-of-social-season event in support of the Canadian Foundation for AIDS Research, when the fund-raising total reached almost $900,000 and attendance climbed to 800. The event, which features dinner parties at Yorkville boutiques and an after-party at the Four Seasons, aims to raise $1 million in 2019. BMO returns as the signature partner. Next: November 27, 2019
Fund-raising grew at last year’s end-of-social-season event in support of the Canadian Foundation for AIDS Research, when the fund-raising total reached almost $900,000 and attendance climbed to 800. The event, which features dinner parties at Yorkville boutiques and an after-party at the Four Seasons, aims to raise $1 million in 2019. BMO returns as the signature partner. Next: November 27, 2019
Photo: Steve Blackburn
11. Waterkeeper Gala

Up from #13
Moving to Hotel X for its lake views, this event in support of water conservation sold out but capped ticket sales at 350 (down from 400) for a more intimate evening. Despite fewer attendees and no silent auction, fund-raising grew to $585,000. Singers Sarah Harmer and Matthew Good performed for the crowd. Next: Spring 2020
Moving to Hotel X for its lake views, this event in support of water conservation sold out but capped ticket sales at 350 (down from 400) for a more intimate evening. Despite fewer attendees and no silent auction, fund-raising grew to $585,000. Singers Sarah Harmer and Matthew Good performed for the crowd. Next: Spring 2020
Photo: Courtesy of Lake Ontario Waterkeeper
12. Ontario Science Centre’s Innovators’ Ball

Up from #15
This gala dinner moves from November to September this year so it can be held on the same date that the Ontario Science Centre opened 50 years ago. The theme for 2019 is “pushing the boundaries of the possible,” and organizers aim to raise $2 million—which would more than double last year’s total—with about 500 attendees. RBC remains the title sponsor. Next: September 26, 2019 See more: 17 Fun, Interactive Ideas From Fall Benefits
This gala dinner moves from November to September this year so it can be held on the same date that the Ontario Science Centre opened 50 years ago. The theme for 2019 is “pushing the boundaries of the possible,” and organizers aim to raise $2 million—which would more than double last year’s total—with about 500 attendees. RBC remains the title sponsor. Next: September 26, 2019 See more: 17 Fun, Interactive Ideas From Fall Benefits
Photo: Nino Liu
13. Scrubs in the City

New to the list
Rio de Janeiro came to Toronto for this lavish fund-raiser for Canada’s foremost children’s hospital, with tickets for 1,400 guests selling out in record time. The gala at the Evergreen Brickworks topped its fund-raising goal of $1 million amid gourmet Brazilian food, living walls, and live macaws. BMO returned as the presenting sponsor. Next: June 11, 2020
Rio de Janeiro came to Toronto for this lavish fund-raiser for Canada’s foremost children’s hospital, with tickets for 1,400 guests selling out in record time. The gala at the Evergreen Brickworks topped its fund-raising goal of $1 million amid gourmet Brazilian food, living walls, and live macaws. BMO returned as the presenting sponsor. Next: June 11, 2020
Photo: Ernesto DiStefano
14. National Ballet of Canada’s Mad Hot Gala

Raising $1.2 million, slighting down from last year, the gala cocktail party drew 1,800 guests to the Four Seasons Centre for the Performing Arts and was presented by CIBC for the 13th year in a row. About 640 guests enjoyed dinner on stage as dancers performed, and the night’s lottery included prizes from Royal de Versailles and Air Canada. Next: June 9, 2020
Photo: Decor and Event Photography
15. Art Gallery of Ontario's Massive Party

This artsy party for the Art Gallery of Ontario capped tickets at 1,500 this year, down from 1,800, and celebrated its 15th, or crystal, anniversary. Organizers entertained guests with performances, art installations, music, and a dose of glitter. Purpose Investments was the lead sponsor. The organization did not disclose a fund-raising total. Next: April 2020
Photo: Tom Hicken
16. Biblio Bash

Up from #18
The gussied-up stacks of the Toronto Reference Library hosted 460 guests and 43 authors for this year’s dinner gala in support of after-school reading clubs and a new bookmobile with free Wi-Fi. Fund-raising was level with 2018, at about $745,000, and TD Bank Group and Toronto Life magazine returned as sponsors. Next: Spring 2020 See more: 10 Best Ideas of the Week: Smirnoff's Pool Float Party, SAP's High-Tech Basketball Court, Budweiser's Lottery Machines
The gussied-up stacks of the Toronto Reference Library hosted 460 guests and 43 authors for this year’s dinner gala in support of after-school reading clubs and a new bookmobile with free Wi-Fi. Fund-raising was level with 2018, at about $745,000, and TD Bank Group and Toronto Life magazine returned as sponsors. Next: Spring 2020 See more: 10 Best Ideas of the Week: Smirnoff's Pool Float Party, SAP's High-Tech Basketball Court, Budweiser's Lottery Machines
Photo: Peter Grande
17. Boobyball

Up from #19
Raising money to fight breast cancer, this youthful party aims to increase its fund-raising total to $500,000 in 2019 when it returns to Rebel nightclub with about 1,800 expected guests. This year’s theme is "Into the Ocean,” and Swedish clothier H&M is back as the presenting sponsor. Next: October 4, 2019 See more: 10 Best Ideas of the Week: a Sugar Flower Art Installation, Jack-O-Lanterns Inspired by Rodeo Drive, Bedazzled Dog Centerpieces
Raising money to fight breast cancer, this youthful party aims to increase its fund-raising total to $500,000 in 2019 when it returns to Rebel nightclub with about 1,800 expected guests. This year’s theme is "Into the Ocean,” and Swedish clothier H&M is back as the presenting sponsor. Next: October 4, 2019 See more: 10 Best Ideas of the Week: a Sugar Flower Art Installation, Jack-O-Lanterns Inspired by Rodeo Drive, Bedazzled Dog Centerpieces
Photo: Courtesy of Rethink Breast Cancer
18. Operanation

A record 180 opera lovers signed up for a V.I.P. pre-party dinner and private performance at the Four Seasons Centre for the Performing Arts at this year’s fund-raiser in support of young opera artists. Total attendance and fund-raising stayed level at 1,000 and $100,000, respectively. Volvo and condo builder Graywood Developments were sponsors. Next: May 2020
See more: 10 Best Ideas of the Week: Swarovski's Bedazzled Ice Pop, a Fairytale-Theme Candy House, Goat Yoga
See more: 10 Best Ideas of the Week: Swarovski's Bedazzled Ice Pop, a Fairytale-Theme Candy House, Goat Yoga
Photo: Gaetz Photography
19. Walrus Gala

Up from #20
For its 15th edition, this gala in support of literacy hosted a capacity crowd that raised $500,000 and included author Margaret Atwood and Toronto Mayor John Tory. The event returned to the Distillery District’s Fermenting Cellar and featured a new house band to keep dancers on their toes. Sponsors included Bombardier and Equitable Bank. Next: January 22, 2020
For its 15th edition, this gala in support of literacy hosted a capacity crowd that raised $500,000 and included author Margaret Atwood and Toronto Mayor John Tory. The event returned to the Distillery District’s Fermenting Cellar and featured a new house band to keep dancers on their toes. Sponsors included Bombardier and Equitable Bank. Next: January 22, 2020
Photo: Ernesto DiStefano
20. Canadian Film Centre Annual Gala & Auction

New to the list
Held in the Ritz-Carlton ballroom for the third year in a row, this star-studded event topped its fund-raising goal to support programs and initiatives in film and television, according to organizers, who did not disclose the total amount raised. About 500 people attended the dinner and auction, taking in live performances and enjoying the Toronto Life augmented-reality photo booth. Netflix was a presenting sponsor. Next: February 20, 2020
Held in the Ritz-Carlton ballroom for the third year in a row, this star-studded event topped its fund-raising goal to support programs and initiatives in film and television, according to organizers, who did not disclose the total amount raised. About 500 people attended the dinner and auction, taking in live performances and enjoying the Toronto Life augmented-reality photo booth. Netflix was a presenting sponsor. Next: February 20, 2020
Photo: T. Sandler